The first one was with my much older girlfriend when I was about 24. She was very into my crossdressing and liked me to be dressed up with her a lot. And she had even convinced me to go for walks with her while I was crossdressed which was a big deal to me since my crossdressing was a secret only a few people knew. So we would park along the beach late enough that it was dark but early enough that there weren’t many people on dates looking to make out or more.
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